Hydrochloric Acid → 6-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 1194105Notes

Reaction equation

HRID 1194105 reaction equation
[CH2:1]=O.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[CH2:8][CH2:9][NH2:10].[ClH:14]>>[ClH:14].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:1][NH:10][CH2:9][CH2:8]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 748663-Methoxyphenethylamine

Product 1

HCID 29203356-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 61%

Procedure

Formaldehyde solution (20%) (50 g) was added dropwise with stirring to 3-methoxyphenethylamine (50 g, 0.33M) over 15 minutes. The reaction was then heated for 1 hour on a steam bath. Excess concentrated hydrochloric acid was added and the mixture was then evaporated to dryness in vacuo. The residual solid was recrystallised from MeOH:isopropanol:ether to yield 6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (41 g, 61%), m.p. 234°-5° C. (lit.* 233°-4° C.).

Workup

  1. temperatureThe reaction was then heated for 1 hour on a steam bath
  2. customthe mixture was then evaporated to dryness in vacuo
  3. customThe residual solid was recrystallised from MeOH

Sources & evidence

ORD record
ord-3471aa2b7a3845ec9390fd8392f3e0f5
Source dataset
uspto-grants-1989_03
Patent number
US04812573

Reaction notes

Loading…